TBAF tetrahydrofuran → N-(4-{2-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide

HRID 1892511Notes

Reaction equation

HRID 1892511 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]2[N:18]=[C:19]([NH:22][C:23](=[O:25])[CH3:24])[S:20][CH:21]=2)[S:9][C:10]=1[Si](C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][C:17]2[N:18]=[C:19]([NH:22][C:23](=[O:25])[CH3:24])[S:20][CH:21]=2)[S:9][CH:10]=1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 86650013HCID 86650013, compound

Product 1

HCID 86650014N-(4-{2-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-{2-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (3.980 g, 10.09 mmol) in tetrahydrofuran (20 ml) was added 1M tetrabutylammoniumfluoride tetrahydrofuran solution (11.1 ml, 11.1 mmol) at room temperature, and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Merck 7734 100 g, ethyl acetate:dichloromethane=1:4→1:2) to give N-(4-{2-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (3.03 g, 9.40 mmol, yield 93.2%) as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (Merck 7734 100 g, ethyl acetate:dichloromethane=1:4→1:2)

Sources & evidence

ORD record
ord-e0b20d3a8272489bad3e67972aa6f86f
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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